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16. Irving "Irv Gotti" Lorenzo, Jr.

One thing is for sure about the enfant terrible of hip-hop, Irving “Irv Gotti” Lorenzo: He would not like that he isn’t #1 on this list.

Irv Gotti, like many producers and A&R reps, made his bones as a DJ for Jay-Z. In the mid 1990s, Gotti gave TVT Records instant authority by bringing them Mic Geronimo and Ca$h Money Click featuring a little-known rapper named Ja Rule. Moving to Def Jam, he facilitated the signing of Jay-Z, and came into his own with the signing of DMX, an artist who yielded two multi-platinum albums in 1998. The self-described “hottest n----a in the building,” Gotti was given his own imprint, Murder Inc., and slugged his grateful masters with the one-two punch of Ja Rule and Ashanti.

Gotti’s increasing profile put him into direct confrontation with Chris Lighty, who left Def Jam shortly thereafter. Lighty’s answer to Gotti, 50 Cent, eventually silenced him. Gotti responded with threats and—if you believe some unconfirmed accounts—actual violence. But one thing Gotti couldn’t manage to do was respond musically.